#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224621.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224621
loop_
_publ_author_name
'Briggs, Jonathan B.'
'Jazdzyk, Mikaël D.'
'Miller, Glen P.'
_publ_section_title
;
 2,3-Bis(bromomethyl)-1,4-diphenylbenzene
;
_journal_coeditor_code           FL2275
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o12
_journal_paper_doi               10.1107/S1600536809050764
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H16 Br2'
_chemical_formula_moiety         'C20 H16 Br2'
_chemical_formula_sum            'C20 H16 Br2'
_chemical_formula_weight         416.15
_chemical_name_systematic
;
2,3-Bis(bromomethyl)-1,4-diphenylbenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.393(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8589(10)
_cell_length_b                   11.5859(13)
_cell_length_c                   16.655(2)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.35
_cell_volume                     1669.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'GIS (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10674
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    4.849
_exptl_absorpt_correction_T_max  0.7936
_exptl_absorpt_correction_T_min  0.1954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.839
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2395
_reflns_number_total             2955
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fl2275.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224621
_cod_database_fobs_code          2224621
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7911(4) 0.0211(3) 0.11822(18) 0.0261(7) Uani d . 1 . .
C C2 0.6744(3) 0.1014(3) 0.12258(18) 0.0251(7) Uani d . 1 . .
C C3 0.6754(3) 0.2110(3) 0.08567(18) 0.0251(7) Uani d . 1 . .
C C4 0.7904(4) 0.2404(3) 0.04258(19) 0.0269(7) Uani d . 1 . .
C C5 0.9077(4) 0.1602(3) 0.04184(19) 0.0296(7) Uani d . 1 . .
H H5 0.9868 0.1787 0.0153 0.035 Uiso calc R 1 . .
C C6 0.9090(4) 0.0545(3) 0.0793(2) 0.0292(7) Uani d . 1 . .
H H6 0.9903 0.0039 0.0788 0.035 Uiso calc R 1 . .
C C7 0.7963(4) -0.0981(3) 0.15312(19) 0.0298(7) Uani d . 1 . .
C C8 0.9294(4) -0.1362(3) 0.2071(2) 0.0408(9) Uani d . 1 . .
H H8 1.0137 -0.0869 0.2219 0.049 Uiso calc R 1 . .
C C9 0.9371(5) -0.2470(4) 0.2389(3) 0.0522(11) Uani d . 1 . .
H H9 1.0268 -0.2716 0.2747 0.063 Uiso calc R 1 . .
C C10 0.8145(5) -0.3204(3) 0.2184(3) 0.0533(11) Uani d . 1 . .
H H10 0.8195 -0.3940 0.2410 0.064 Uiso calc R 1 . .
C C11 0.6828(5) -0.2845(3) 0.1635(3) 0.0530(11) Uani d . 1 . .
H H11 0.5999 -0.3348 0.1483 0.064 Uiso calc R 1 . .
C C12 0.6736(4) -0.1744(3) 0.1314(2) 0.0419(9) Uani d . 1 . .
H H12 0.5843 -0.1511 0.0947 0.050 Uiso calc R 1 . .
C C13 0.7925(4) 0.3495(3) -0.0039(2) 0.0312(7) Uani d . 1 . .
C C14 0.7961(4) 0.4578(3) 0.0321(2) 0.0380(8) Uani d . 1 . .
H H14 0.7928 0.4636 0.0874 0.046 Uiso calc R 1 . .
C C15 0.8044(5) 0.5578(4) -0.0128(3) 0.0512(11) Uani d . 1 . .
H H15 0.8063 0.6294 0.0125 0.061 Uiso calc R 1 . .
C C16 0.8098(5) 0.5512(4) -0.0940(3) 0.0532(11) Uani d . 1 . .
H H16 0.8150 0.6181 -0.1241 0.064 Uiso calc R 1 . .
C C17 0.8075(5) 0.4442(4) -0.1311(3) 0.0562(12) Uani d . 1 . .
H H17 0.8118 0.4392 -0.1863 0.067 Uiso calc R 1 . .
C C18 0.7989(4) 0.3441(4) -0.0863(2) 0.0429(9) Uani d . 1 . .
H H18 0.7974 0.2726 -0.1119 0.051 Uiso calc R 1 . .
C C19 0.5527(4) 0.0732(3) 0.16939(19) 0.0300(7) Uani d . 1 . .
H H19A 0.5369 0.1395 0.2022 0.036 Uiso calc R 1 . .
H H19B 0.5883 0.0097 0.2066 0.036 Uiso calc R 1 . .
C C20 0.5528(4) 0.2970(3) 0.0926(2) 0.0333(8) Uani d . 1 . .
H H20A 0.4540 0.2581 0.0866 0.040 Uiso calc R 1 . .
H H20B 0.5441 0.3538 0.0491 0.040 Uiso calc R 1 . .
Br Br19 0.35394(4) 0.03039(4) 0.09650(2) 0.04810(18) Uani d . 1 . .
Br Br20 0.60479(5) 0.37511(4) 0.20073(3) 0.05089(18) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.2(3) ?
C6 C1 C7 . . 118.2(3) ?
C2 C1 C7 . . 123.6(3) ?
C1 C2 C3 . . 120.0(3) ?
C1 C2 C19 . . 120.2(3) ?
C3 C2 C19 . . 119.7(3) ?
C2 C3 C4 . . 120.8(3) ?
C2 C3 C20 . . 119.5(3) ?
C4 C3 C20 . . 119.7(3) ?
C3 C4 C5 . . 117.6(3) ?
C3 C4 C13 . . 124.3(3) ?
C5 C4 C13 . . 118.0(3) ?
C6 C5 C4 . . 121.6(3) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
C5 C6 C1 . . 121.6(3) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
C8 C7 C12 . . 118.3(3) ?
C8 C7 C1 . . 119.6(3) ?
C12 C7 C1 . . 122.0(3) ?
C7 C8 C9 . . 120.4(4) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C10 C9 C8 . . 120.7(4) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 119.4(4) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C10 C11 C12 . . 120.4(4) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C7 C12 C11 . . 120.7(4) ?
C7 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C18 . . 117.8(3) ?
C14 C13 C4 . . 123.1(3) ?
C18 C13 C4 . . 119.0(3) ?
C13 C14 C15 . . 121.3(4) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C16 C15 C14 . . 120.3(4) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 119.5(4) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C18 C17 C16 . . 120.3(4) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C13 . . 120.8(4) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
C2 C19 Br19 . . 112.4(2) ?
C2 C19 H19A . . 109.1 ?
Br19 C19 H19A . . 109.1 ?
C2 C19 H19B . . 109.1 ?
Br19 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C3 C20 Br20 . . 110.1(2) ?
C3 C20 H20A . . 109.6 ?
Br20 C20 H20A . . 109.6 ?
C3 C20 H20B . . 109.6 ?
Br20 C20 H20B . . 109.6 ?
H20A C20 H20B . . 108.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.397(5) ?
C1 C2 . 1.403(5) ?
C1 C7 . 1.496(5) ?
C2 C3 . 1.412(4) ?
C2 C19 . 1.496(5) ?
C3 C4 . 1.408(4) ?
C3 C20 . 1.497(4) ?
C4 C5 . 1.396(5) ?
C4 C13 . 1.485(5) ?
C5 C6 . 1.373(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.392(5) ?
C7 C12 . 1.387(5) ?
C8 C9 . 1.385(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.364(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.382(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.388(5) ?
C13 C18 . 1.387(5) ?
C14 C15 . 1.389(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.366(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.384(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.390(6) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 Br19 . 1.976(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 Br20 . 1.979(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12 Br19 . 0.93 2.93 3.644(4) 134
C20 H20A Br19 . 0.97 2.80 3.563(4) 136
C14 H14 Br20 . 0.93 2.96 3.704(4) 139
C19 H19A Br20 . 0.97 2.80 3.552(4) 135
C19 H19B Br20 2_645 0.97 2.98 3.632(4) 126
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.2(4) ?
C7 C1 C2 C3 . . . . -178.0(3) ?
C6 C1 C2 C19 . . . . -175.1(3) ?
C7 C1 C2 C19 . . . . 4.8(4) ?
C1 C2 C3 C4 . . . . 1.5(4) ?
C19 C2 C3 C4 . . . . 178.8(3) ?
C1 C2 C3 C20 . . . . -178.4(3) ?
C19 C2 C3 C20 . . . . -1.1(4) ?
C2 C3 C4 C5 . . . . -3.6(4) ?
C20 C3 C4 C5 . . . . 176.3(3) ?
C2 C3 C4 C13 . . . . 174.6(3) ?
C20 C3 C4 C13 . . . . -5.5(5) ?
C3 C4 C5 C6 . . . . 2.1(4) ?
C13 C4 C5 C6 . . . . -176.2(3) ?
C4 C5 C6 C1 . . . . 1.6(5) ?
C2 C1 C6 C5 . . . . -3.7(5) ?
C7 C1 C6 C5 . . . . 176.4(3) ?
C6 C1 C7 C8 . . . . 53.1(4) ?
C2 C1 C7 C8 . . . . -126.8(3) ?
C6 C1 C7 C12 . . . . -124.8(4) ?
C2 C1 C7 C12 . . . . 55.3(4) ?
C12 C7 C8 C9 . . . . -1.0(5) ?
C1 C7 C8 C9 . . . . -179.0(3) ?
C7 C8 C9 C10 . . . . -0.3(6) ?
C8 C9 C10 C11 . . . . 1.6(6) ?
C9 C10 C11 C12 . . . . -1.6(6) ?
C8 C7 C12 C11 . . . . 1.0(5) ?
C1 C7 C12 C11 . . . . 178.9(3) ?
C10 C11 C12 C7 . . . . 0.2(6) ?
C3 C4 C13 C14 . . . . 58.9(4) ?
C5 C4 C13 C14 . . . . -122.9(4) ?
C3 C4 C13 C18 . . . . -124.3(3) ?
C5 C4 C13 C18 . . . . 53.9(4) ?
C18 C13 C14 C15 . . . . 0.5(5) ?
C4 C13 C14 C15 . . . . 177.3(3) ?
C13 C14 C15 C16 . . . . -0.2(6) ?
C14 C15 C16 C17 . . . . -0.2(6) ?
C15 C16 C17 C18 . . . . 0.4(6) ?
C16 C17 C18 C13 . . . . 0.0(6) ?
C14 C13 C18 C17 . . . . -0.4(5) ?
C4 C13 C18 C17 . . . . -177.3(3) ?
C1 C2 C19 Br19 . . . . -103.0(3) ?
C3 C2 C19 Br19 . . . . 79.7(3) ?
C2 C3 C20 Br20 . . . . 80.7(3) ?
C4 C3 C20 Br20 . . . . -99.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10820871
